Mike comes on the show for a 3rd time to give us a progress report on how he is making his Hollywood dream come true. We chat about getting comfortable with the uncomfortable, making a plan, and having fun with learning.

After being on episode 34 - Marketing your own product line - Krissy comes back to tell us how things are going. She initially was concerned about telling her story about being a massage therapist when trying to sell her new sleep products, as she wanted to be taken seriously as an entrepreneur. We learn that the more you get used to talking about what you love, the more you can talk about it to anyone, and that getting a mentor is invaluable.

Helena returns after being on episode 32 on how to pursue multiple interests with a creative career. Her original concern was that if she pursued one interest, all the rest of the creative dreams would fall behind. She said that my advice about seeing all the pursuits as part of a whole — where each feeds into each other instead of each being separate — helped her calm down, accept where she was, and feel stronger by knowing what she could control.

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William Green, financial journalist, ghost writer, and author of books such as Richer, Wiser, Happier, talks about his insights on why life gets hard, how to look at a challenge like writing a book, and shares some of the wisdom he's learned from the financial gurus he's interviewed over the decades on how to face adversity.

Isyemille returns after being on episode 21 about how to make money from making art. I explained that to do so, she had to build a connection with an audience. She shares that in her journey she learned something more important than making money: that the act of creating is priceless.

Mike returns after being on episode 38 to share if any of the advice I gave him worked - looking at switching careers as dream hunting instead of job hunting. His insights into setting goals, being happy, and understanding passion reveal the truth that sometimes when it looks like we're trying solve one problem, we're actually solving another one with even better results.

Kameron is a multi-talented artist who also helps other artists navigate their creative careers, but is looking for better ways to create an impact that pays. I explain that it's about connecting the dots between brand, audience and purpose that helps attract the kind of business partnerships that he might like.

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Anthony Roth Costanzo is an opera singer and producer who has led performances at opera companies worldwide. He's performed in musical theater, plays, operas and movies since he was 11 years old. We talk about understanding your creative purpose when the work being made can seem small compared to real-world problems, or if you're just feeling directionless. The answer: Empathy.

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Rebecca Rumble is Creative Director at Squarespace, a go-to for creators and solopreneurs building their websites and e-commerce platforms. She quickly rose up the ranks in her career, working on big brands at tony shops both Stateside and internationally. She talks candidly about burnout and using mental space as a tool to stay strong on any creative journey.

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Alexandra has always been able to find jobs because she's well connected, or has lots of friends, but now that she's starting a new career, she wants to leverage her network more effectively for particular career goals. I explain that it's about making people in her network feel important.

shoeate.com and Instagram @shoeatewisewords